NP-MRD: Showing NP-Card for 5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one (NP0327282)

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Record Information

Version

2.0

Created at

2022-09-12 09:43:18 UTC

Updated at

2022-09-12 09:43:18 UTC

NP-MRD ID

NP0327282

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one

Description

5-(10,10-Dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one is found in Xestospongia testudinaria. 5-(10,10-Dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231518102D          

 19 19  0  0  0  0            999 V2000
    0.7650   -3.4047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4795   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9084   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4808   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4808   -3.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953   -3.8172    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -3.8172    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7031   -2.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551   -1.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426   -1.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782   -0.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -1.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C=CCCCCCC=C(Br)Br)C1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20Br2O3/c15-13(16)8-6-4-2-1-3-5-7-11(17)12-9-10-14(18)19-12/h5,7-8,11-12,17H,1-4,6,9-10H2

> <INCHI_KEY>
CHSPIILKMVACOK-UHFFFAOYSA-N

> <FORMULA>
C14H20Br2O3

> <MOLECULAR_WEIGHT>
396.119

> <EXACT_MASS>
393.977921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.78952295892476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
4.1147262143333325

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.809862400238487

> <JCHEM_PKA_STRONGEST_BASIC>
-3.319366186135686

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
94.0245

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       1.428  -6.356   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.428  -4.816   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.762  -4.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.095  -4.816   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.429  -4.046   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.763  -4.816   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.096  -4.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.430  -4.816   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.764  -4.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.097  -4.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.097  -6.356   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0      13.431  -7.126   0.000  0.00  0.00          Br+0
HETATM   13 Br   UNK     0      10.764  -7.126   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       0.094  -4.046   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.312  -4.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.343  -3.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.573  -2.194   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.199  -0.787   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.067  -2.514   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀Br₂O₃

Average Mass

396.1190 Da

Monoisotopic Mass

393.97792 Da

IUPAC Name

5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one

Traditional Name

5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one

CAS Registry Number

Not Available

SMILES

OC(C=CCCCCCC=C(Br)Br)C1CCC(=O)O1

InChI Identifier

InChI=1S/C14H20Br2O3/c15-13(16)8-6-4-2-1-3-5-7-11(17)12-9-10-14(18)19-12/h5,7-8,11-12,17H,1-4,6,9-10H2

InChI Key

CHSPIILKMVACOK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xestospongia testudinaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketene acetal or derivatives
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Bromoalkene
Vinyl bromide
Vinyl halide
Haloalkene
Organohalogen compound
Organobromide
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.47	ALOGPS
logP	4.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	33.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one (NP0327282)

MOL for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

3D MOL for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

3D SDF for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

3D-SDF for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

PDB for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

3D PDB for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

SMILES for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

INCHI for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

Structure for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)

3D Structure for NP0327282 (5-(10,10-dibromo-1-hydroxydeca-2,9-dien-1-yl)oxolan-2-one)